Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Framework For Hiring The Best Talent 100% Remotely, Raising $32M From Benchmark and GV Pre-Launch and How To Think Through Capital Efficiency and Runway Today with Jeff Seibert and Wayne Chang, Co-Founders @ Digits About this episode Wayne Chang and Jeff Seibert are the co-founders @ Digits, the company that gives you a complete, real-time understanding of your expenses, all in just a few clicks. To date, Wayne and Jeff have raised over $32M for Digits from some of the best in the business including Peter Fenton @ Benchmark and Jess Verrilli @ GV and then with the most incredible base of angels with the founders from Box, Github, Stitch Fix, Tinder, Gusto and more. Prior to Digits, Wayne and Jeff co-founded Crashlytics, acquired by Twitter for a 9-figure sum in Jan 2013 and then acquired from Twitter by Google in 2017. If that was not enough they are also LPs in some of the world's most exclusive funds and angels in the likes of Gusto, OpenDoor and SoFi to name a few. In Today’s Episode You Will Learn: 1.) How did Jeff and Wayne make their way into the world of tech and startups? How did Wayne crashing a startup dinner start everything for them? 2.) How did Jeff and Wayne's prior success with Crashlytics impact their operating mindset scaling Digits today? What worked? What did not work? What gets easier with time? What gets harder the second time around? 3.) What have been Wayne and Jeff's biggest lessons from having a remote team from Day 1? What structure and framework do they use to hire the best remote talent? How does that change at the exec level? How do they think about optimising product management for remote teams? 4.) How would Wayne and Jeff summarise their design philosophy with Digits? Why does Wayne believe "minimalism only favours the designer"? When does it make sense to actually add some complexity to your product? 5.) Digits raised $33M pre-launch, why did they favour this approach? How do they think about when to transition from lean and iterative to aggressive and pouring fuel on the fire? Why did they choose to work with Peter Fenton? How do they think about optimising their angel network? Items Mentioned In Today’s Show: Wayne’s Fave Book: Enders Game Jeff's Fave Book: Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs As always you can follow Harry and The Twenty Minute VC on Twitter here!
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? We are back on the 20 minute VC and Founders Friday with me, Harry Stebbings, and straight into the episode today, but I had the chance to interview these two incredible founders separately in the past. They've since become friends and been incredibly kind to me. And with their new round and public launch last week, I thought now might be the perfect time to have them back on the show, this time together. And so with that, I'm thrilled to welcome back to the hot seat Jeff Seibert and Wayne Chang, co-founders at Digits, the company that gives you a complete, real-time understanding of your expenses, all in just a few clicks. To date, Wayne and Jeff have raised over $32 million for Digits, from some of the best in the business, including Peter Fantin at Benchmark and Jess Verilli at GV, and then also the most incredible base of angels, with the founders from Box, GitHub, Tinder, Gusto, and more.
0:42 Harry Stebbings? Prior to Digits, Wayne and Jeff co-founded Crashlytics, which was acquired by Twitter for a nine-figure sum in January 2013, and then acquired from Twitter by Google in 2017. I do also want to say a huge thank you to Jess at GV for some fantastic question suggestions today. I really do so appreciate that, Jess. But before we move into the show today, I'm sure you've heard about it, but my word, this is a product I love, Carter. Carter simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to Carter.com/20VC to get 10% off. More than 800,000 employees and shareholders use Carter to manage hundreds of billions of dollars in equity, and Carter now offers fund administration, so you can see real-time data in the Carter platform and work with Carter's team of experienced fund accountants.
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3:00 Speaker 01 You have now arrived at your destination.
3:03 Harry Stebbings? Chaps, what can I say? I've had you both on the show separately. It's been an amazing few years since our last episodes, but thank you both so much for joining me today.
3:10 Speaker 02 Welcome. Happy to be here.
3:12 Harry Stebbings? I mean, God, you're practically finishing each other's sentences already. You must be co-founders, chaps. I do want to kick off today though with a little bit of context. So it's super brief, but it hit me. I love a good romance story. So how did you guys come together and how did you come to found Digits?
3:25 Speaker 03 So believe it or not, Jeff and I met at a startup dinner in Boston back in 2011 and it was at a dinner that I wasn't even invited to.
3:33 Speaker 02 Yeah, I can't believe you crashed that, but I guess lucky in retrospect.
3:37 Speaker 03 Yeah. And long story short, we ended up starting Crashlytics together. Just over 12 months after launch, we hit 300 million IMUs and then Twitter acquired us. So now happy to say that Crashlytics runs on 5 billion monthly active devices required by Google.
3:52 Speaker 02 We had an just absolute blast building that company and at Twitter spent sort of the first half the time on the developer platform side. And then I became head of consumer product for Twitter in 2015. And we always knew though that we wanted to get back to startups. We loved building stuff together. And in particular, we love building really highly designed software for really unsexy spaces. And so as we started thinking about projects to tackle, one of the frustrations we had At Crashlytics was we felt like we never had any visibility into our finances. Like, working with our accountant was quite frustrating. You had to wait weeks after the end of each month to get any report. And we really had no idea where we were spending money, what our runway looked like, et cetera. And so that's our new focus.
4:35 Speaker 02 We've sort of become obsessed with solving this in the form of digits.
4:38 Harry Stebbings? I mean, I absolutely love that in terms of the founding story in that aha moment. And do not worry, if I had to be invited to all the dinners that I go to, I'd probably never go to any dinners. But reassuring to hear that. I do want to start there and kind of a lovely element for any investor working with you today. They know that, as you said there with Crashlytics, you've already been incredibly successful as a founding pair. And those prior experiences, they do impact how you think about operating today. So how did the prior experiences with Crashlytics in particular, I guess, impact your operating mentality today, do you think?
5:06 Speaker 02 Yeah, very directly. So if you look back to 2011, nobody at that time was putting the words developer tools and easy to use in the same sentence. Like, that was not a thing people thought about. And we took a huge bet, honestly, that taking a really design-first approach to such a deeply technical product would make it far more accessible and ideally far more usable by a much larger audience.
5:29 Speaker 03 Yeah, I have a quick funny story. I was at a dinner last year in L.A. And, you know, another, another group put it together. Next to me was Chamillionaire. And so we did a round of intros. And then later in the evening, there's a little tap on my right and it's him. And he's showing me his phone and there's a Crashlytics alert on it. And he's telling me how excited he is because he's launching a new app. And that was a really cool moment for me because I remember growing up and listening to Chamillionaire. And here he is, he's showing me Crashlytics on his phone to me.
5:58 Harry Stebbings? I mean, that is, that is a career highlight when Chamillionaire does that. And it's so cool.
6:02 Speaker 02 It was that approach of like, hey, could we totally democratize developer tools that we're now taking here? And so it's sort of the same mentality, right? Like, financial software has existed for decades. Nobody ever thinks of it as delightful or easy. And so we've really set off with this same approach. Like, what if we took a design-first mentality when it came to the sort of arcane world of business finance? And what if the entire premise of digits was that you didn't need a background in finance or accounting in order to use it? And sort of The moment you start with that, then a ton of the architecture and design decisions just sort of fall into place.
6:35 Harry Stebbings? Can I just ask, you know, it's one thing that's very striking when you look at the digits offering state is like the element of time to value and it being so fast. How do you think about the importance of time to value?
6:45 Speaker 02 It's honestly essential and this is what Wayne has taught me. I mean, why don't you dive in?
6:49 Speaker 03 Yeah. So, I mean, a lot of companies, they think about just solving for that problem, but that's just a small piece of it. So no matter what problem that it is that we're solving, whether it's like crash reporting or financial reporting now, it can be so much better than what it currently is. All the tools are available today. It doesn't have to be that way. So we've spent an enormous amount of time on the onboarding experience, for example. And so to like, to give a quick perspective, that small thing of saying the onboarding experience, our competitors, other people that are in the space, they're out there and they're touting that it's so quick to set up. They can get set up in as little as 16 weeks. And that's weeks. That's one of the fastest we found. Others take months or like as little as 14 months.
7:30 Speaker 03 So it's 2020. That doesn't have to be the norm. And so we're set out to improve that. We want this to be just a few clicks. And after many years of development, we've innovated in that spot and that's one of the things that we've done.
7:42 Harry Stebbings? Yeah, it's been amazing to see. I guess the other question I have is like, if you think about that very design first in the unsexy industry is kind of a core thing that worked really well. Are there any other elements, maybe specifically around kind of company building that worked really well with Crashlytics that you've definitely carried over now with you to digits?
7:58 Speaker 02 I would say just sort of repeating Wayne, an end to end focus on the customer. I think one thing that works really well for us is many companies as they grow, get distracted by sort of internal politics and reporting structures and where the idea came from. And one of the things we were always very disciplined at with Crashlytics was it's the customer that matters. The rest of it, the entire structure of the company is there only to deliver value to that customer. And so we were very disciplined not to allow our focus to shift towards sort of internal things. The focus of every week was, hey, what are we delivering for customers this week and how can we make their lives better? And that just sort of aligns everyone and reduces all the other drama. It's just. About building and delivering customer value.
8:42 Harry Stebbings? Totally with you. I think that kind of maniacal focus around the customer is so clarifying in terms of prioritization. If that's what worked, on the flip side, maybe tougher to say. What didn't work with Crashlytics that maybe you won't be carrying over to Digits? And why don't you think it worked?
8:55 Speaker 02 We've taken a totally different technical approach this time. And to set the context, Crashlytics was very organic. I wrote it as a side project. I wrote it in Ruby on Rails. And it was fast to get up and running, but a huge struggle for us to scale. And so we ended up rewriting major pieces of it just in the first year as we got to 300 million devices. Then, of course, most of it over the next two years as it reached billions of devices. And because of all that effort, we actually couldn't build the features we wanted to. We were sort of changing out the engine of the car repeatedly without adding any new capabilities. And so with Digits, we had now seen that movie. And we wanted to bake a lot of that in from the beginning. So we're building financial software. We take that responsibility extremely seriously.
9:40 Speaker 02 So it has to be secure, it has to be correct, and it has to scale. And so we've been really disciplined in choosing a tech stack that's type safe end to end. We use encryption everywhere. We've architected it from the start to be microservices that interconnect and can scale separately. And so the downside is it's longer to get up and running. There's a lot more we've had to build this time around. It would have been much faster to throw together a Rails app. But we knew from day one at Digits that we were committed to this for the long haul. And now we're sort of in a fortunate position where we have the technical foundations laid to support that mission.
10:13 Harry Stebbings? Yeah, no, listen, I'm totally with you there. I think absolutely building for the long term. I always say kind of go slow to go fast. So totally with you there. I do want to touch on another really interesting element, though, that you decided on from day one with Digits, which is the remote team element and obviously incredibly pertinent today with COVID-19. And so I want to dive into this bluntly, chaps. How's it working for you?
10:32 Speaker 03 Oh, for me, working remote is fantastic. It's very, very results oriented, so it's not process oriented. So all that fluff about offices, they just go away. So at the macro level, all that remains is a team, the product, and a company that we're all building together. Working remotely is much more productive. I would say it's more Productive in my career.
10:50 Harry Stebbings? Yeah, no, listen, I totally agree with you. I think taking out the office is the biggest headache in the world. There are always challenges, though, especially when you're doing it wholesale and also for the first time. What were some of the biggest challenges or maybe teething problems in the early days? And I guess, how did you overcome them?
11:04 Speaker 02 Yeah, so from our experiences at Twitter, we had teams across half a dozen offices that I was running. And we were very convinced engineering would be fine. We knew how to run remote engineering teams. That was okay. The unknown, honestly, to us was the product side. We had a lot of doubts of how do you do product management remotely? How do you brainstorm? How do you whiteboard? How do you collaborate in a way that we felt would be productive? And so we struggled, I'd say, quite a bit with this for the first six months of digits. And Wayne and I even had to finally come to an agreement where either I would fly down to visit him in L.A. Or he would come up to San Francisco and we'd do that every other week so that we could get enough product time together. And then, crazily enough, we solved it.
11:44 Speaker 02 So we found out about this app called Pixelboard and we both bought iPad Pros. And this was 18 months ago, and I don't think I've been to L.A. since. And it's really crazy. And so what it is, is it's a real-time whiteboarding app. You jump on an audio chat together, fire up the app, you can draw live, etc. But that part's obvious. I think the core realization that they had is that most of the time you're collaborating around a whiteboard, you're not actually drawing, right? You're standing there, you're thinking, you're gesturing. And remotely, it's the gesturing that gets lost. And what Pixelboard did is they nailed lightweight gesturing. You can switch to a sort of a magic wand tool and you can circle things, draw arrows, underscore, emote, do whatever you want. And after a few seconds, it just delightfully fades away.
12:29 Speaker 02 And that little piece of user interaction literally changed everything for us. And we can now do product brainstorms, wireframing discussions, sketching out new ideas, sketching out new marketing pages, completely remotely. And that's just been game-changing.
12:44 Harry Stebbings? I mean, I absolutely love that. And I'm sure they'll see some pretty noticeable uptick, having heard that from you guys on this episode. I do have to ask, though, because like one challenging thing I think a lot of people find, and I'm sorry, this is off-schedule, but it's actually kind of the mental health that sometimes remote work can induce, and it being maybe more lonely than imp. How do you guys think about building that internal morale and preventing that loneliness? We do internal daily meetings and quite frankly, they're a fucking pain in the ass. But what's the solution in your mind to that more soft interpersonal skills?
13:14 Speaker 02 Yeah, I think you need to have a real discipline around building community as a team and building touchpoints. So we don't do it daily, that's great to know, but we've found every forty eight hours works well. So we do a checkpoint Monday morning, Wednesday morning, Friday, and that allows the whole team to see everyone. And these are all hands, right? And so that allows you to see everyone's face on the screen. You can see what's going on, understand what works being done, what the company is. But you need to find ways for people to connect directly and casually too throughout the experience. I don't know, Wayne, do you have thoughts?
13:46 Speaker 03 Yeah, it's really important that everyone doesn't have just Zoom meetings just blocked out throughout the day. That's the worst way to work remote. That means you're basically replacing the best of remote, which is your ability to form around the objectives, with the worst of being offices, which is endless meetings. And now you're translating those endless meetings into remote environment and you're blockading all of your available creative time, which is endless Zoom meetings. We don't do that. We only have three meetings a week that are required and the rest you get to pick. You get to decide the format and it's very ad hoc, very organic. That is a game changer. And so seeing companies now on Twitter and they're just talking about Zoom meeting after Zoom meeting, that's doing it wrong. That's not the right way to work remotely, in our opinion.
14:29 Speaker 02 Let me just explain how we do that. And I think this is a really key realization we've had is that because most companies, and of course, while we were at Twitter, you're in back to back meetings all day, every day. The biggest realization is that the moment the company is fully remote, you don't own a conference room, which means you don't need to book it, which means the meeting doesn't need to be planned in advance to book the room, which means it doesn't have to be half an hour, an hour long. And so I would say Wayne's exactly right. We have those three meetings and then nothing else on the calendar and everything else is ad hoc. And so I'd say our average meeting length is probably five to seven minutes. The way this works is we do what's called a buddy system. So every project every week is tackled by two. People, some two to four people, but usually two people.
15:12 Speaker 02 And the reason is, it's because you're remote, right? Instead of sort of working by yourself in your room or in your coworking space, now you actually have someone at the company you're working with. And so our pairs basically work on their work together synchronously on audio or video chats. And that gives you this huge social component that you would miss otherwise from not being in an office. And so the work within the buddies is synchronous, they're doing it together. The work between the different teams is asynchronous. You communicate through docs or cards or chat. And that's how you can get away with not having any other scheduled meetings.
15:46 Harry Stebbings? And listen, I love that in terms of the buddy system. Again, another one off schedule, so I'm really sorry for this, I'm just too intrigued. Obviously, helping portfolio companies hire, especially kind of execs today, it's more challenging than ever because we're not used to fully remote end-to-end hiring, especially when it comes to like execs. How did you approach building out the team and ensuring that super high quality when done entirely remotely?
16:06 Speaker 02 Yeah, that has definitely been a big focus for us as well. So we look at it in two sides. It's basically, do you have the skills to do the work? And then what is your style of work? How do you work with other people? And for the skill side, we have used basically a take-home work sample, a take-home challenge that we use for every single role. Of course, for engineering, it's a technical challenge. For our customer concierge team, it's how do you communicate with customers? How do you think about phrasing emails and language and building relationships remotely? So there's a work sample component. And then on the how you work, we use a technique called top grading to do a really thorough exploration of each candidate's background. And we have just been floored by the signal that provides us. And so we've actually been able to make offers fully remotely,
16:49 Speaker 02 never having met the candidate in person, with very high conviction that we sort of understand them and know how they work and know how they fit into teams. Of course, obviously, sometimes a mistake happens. We have let one person go in the life of the company, but it's just one. And overall, it's been a very, very effective way to build a very highly performing team.
17:07 Harry Stebbings? To be fair, I deserve to get five, I was out of shit, I totally understand, guys.
17:13 Harry Stebbings? I'm sorry, I'm too intrigued. What's top grading? I've never heard of this before.
17:16 Speaker 02 Yeah, it is an interview practice where you basically ask the same set of questions around every item in the person's resume. So for the job they had prior, who was your boss? What did they think of you? What were your strengths and weaknesses? What would your team say your strengths and weaknesses are? Those types of things. And you can Google it for people watching. You can Google it. There's a script online. And it's just because it's formulaic and you're asking the same questions for each job role, you can very easily see patterns over a person's career.
17:45 Harry Stebbings? That's fascinating and I'll include links in the show notes. So absolutely, if you're hearing this, you can find that on the site. I do want to ask guys, because you know, now obviously everyone's remote. It's more conventional and I hope more conventional wisdom to build remote-first companies. There are other elements which you have done very uniquely at Digi. So first is when we come to product, we chatted before and you said minimalism favors the designer. Can I ask, what did you mean by this? And how does that play into how you think about product building and product experience?
18:11 Speaker 03 Ever since Apple introduced iOS back in 2013, it feels like the software world has moved more and more towards minimalist design. And so that means like, you know, the more lines and shapes and colors and textures you can remove from the user experience, the better. And I don't think users really care about what is the trendiest design philosophy of the day. When I do the product experiences at Digi and different flows and different things to think about, I'm building product experiences that try to give the users the best experience with the least amount of thinking, the lowest cognitive load. So these result in being the most magical for them when we think about it from that frame. And so when I frame the product in that way, sometimes like being minimalism may work in that moment, but most often it does not. It tends towards maximalism. And for me, that's okay.
18:56 Speaker 03 It doesn't really matter if it's minimalism or maximalism. We ultimately care about building products that are intuitively easy to use. And so we use all kinds of design perspectives to do that. With Digi, no one has ever built full-color visually immersive financial software. And we've done quite a lot of work on this. So I'm really excited to have more of our customers' experience. What we've built so far.
19:18 Harry Stebbings? Can I ask, we had David Heinemeier from Basecamp on the show and, you know, an opinionated chap to say the least. But he mentioned about Zoom and he mentioned we have a generation and actually Rahul at Superhuman agreed with him. He said, we've got a generation of product managers who are inherently focused on minimalizing the number of clicks that we do and they spend hours and hours and hours procrastinating on taking it from four clicks to three clicks. Would you agree in terms of this generation of product designers? And I guess, how would you advise them with this kind of willingness towards maximalism in mind?
19:47 Speaker 03 Yeah, I mean, that's a very myopic view, I think, of product design is like reducing amounts of steps. Sometimes the right answer is increasing the amount of steps. Sometimes by reducing the number of clicks, the user may lose context. They might not know why. And so you're missing opportunities of delight. So being just focused on number of clicks, I think misses the point. We should be designing around the users and the humans that are using our tools, not just by the number of clicks that exist. And so, yeah, sometimes the answer for maximizing user experience might be reducing clicks. Other times, it may be probably more context. Maybe it's an additional screen. Maybe it's something else that means an email that they get, or maybe something else. But just the dimension of reducing clicks, I don't think will result in the best user experience.
20:29 Harry Stebbings? Can I ask another question? Sorry, this is just kind of quite blunt, but it's like when you look at innovation and kind of the financial tools market that we have today, as you said that in terms of the color palettes that you use and in terms of how you approach products, why has no one approached it with this fresh mindset before Bluntme?
20:43 Speaker 03 They've been using these black and white spreadsheet papers forever, and it's a gift that keeps on giving. Unfortunately, you have these archaic reports that aren't super actionable, especially in the moment. In this day and age when we need to react in the moment, in the second, receiving reports will be not that great. And so if you're innovating from the perspective of, oh, maybe I can get you reports just a little bit faster, that's asking for a faster horse. That's not asking for a brand new approach to why are we receiving these reports in the first place?
21:14 Speaker 02 Just an anecdote for you. So we've done a ton of customer development work and we were speaking with a CFO last summer. And we're talking through typical needs, requests the finance department gets. And I asked him, oh, so, okay, so what if I wanted to view employee expenses related to travel, broken down by category, by quarter, okay, great, by employee name? And then he stopped and took a step back and was like, no, I can't give you that report. And I was like, why not? And he said, well, it's three dimensional. I can't print that. And that realization that so much of this world has been guided by what can be physically printed, like, we can throw that out the window.
21:52 Harry Stebbings? Yep, no, this is, I totally agree. And it's an interesting anecdote to hear. I guess the other kind of really interesting element is also how you've approached fundraising, because maybe not the traditional, you know, raising close to thirty three million dollars pre-launch. Can I ask, why did you favor this approach? And what's been the benefits of the strategy you've chosen, do you think?
22:09 Speaker 02 So it's really critical, I believe, to shape your fundraising approach based on the vertical you're in and the sort of current market dynamic. And I'm not sure enough founders really pay attention to this. So at Crashlytics, we took an incredibly cash-constrained approach, because we were conscious, honestly, of the challenges of the developer tool space. And so for that company, we only ever raised six million in funding. We only ever spent three million of it before the acquisition. We gave the rest back to shareholders during the acquisition. And a few of our competitors actually raised way too much, and that prevented them from ever achieving a successful outcome, unfortunately. And so for digits, how should we approach this? Well, we knew from the beginning that the space was massive and we wanted to be in this for the long haul. We aren't looking for a quick flip. We've seen an acquisition already.
22:52 Speaker 02 And we want to meaningfully change the face of financial software worldwide. So that's not a short-term play. And so knowing that and knowing that the markets would likely turn at some point, we took advantage of the eager funding environment over the past couple of years and honestly went out to secure what we'll need to go build the business. And so I think the key differentiator here is, yes, we've raised thirty three million. We aren't spending it. The big mistake people make is they scale their burn sort of in proportion to their raise. And we haven't. We've kept our team super small and lean. We've kept our burn as minimal as possible. We're now sitting on over 10 years of runway. So we're in a good position, not only to serve this sort of current uncertainty, but survive it and then build this company.
23:33 Harry Stebbings? Can I ask, you mentioned the conservancy there and really being so lean. How do you think about when's the right time to really pour fuel on the fire? And switch that mindset from lean and kind of very iterative to actually full gung ho. We're going to deploy capital aggressively. What's that transition?
23:48 Speaker 02 Yes, sign of product market fit. So while you were in an uncertain phase, while you're sort of proving out the concept, I would be extremely conservative with spend because you want to preserve optionality in the case you do need to pivot. We've been now in a fortunate position that the launch has been received very, very well. We're being inundated with signup requests. And so over the next few months, we will begin scaling the team more in order to take advantage of the market opportunity. But I think that's really risky to do prematurely.
24:16 Harry Stebbings? Yeah, I totally agree with you. You did also choose Peter Fenton to work with from the first round with Benchmark. Peter is probably my man crush of venture and I was thrilled to see that, obviously. But why did you choose Peter? You could have chosen anyone. Why did you choose Peter?
24:28 Speaker 02 So we've known Peter for over a decade. He was actually my randomly assigned mentor in a Stanford class in 2007. And I had sort of been looking for an opportunity to work with him ever since. He's just very much impressed me with his intuition, with his insights in how you build businesses. And so when the opportunity arose this time around to work with him on digits, it was a no brainer.
24:51 Harry Stebbings? Yeah, no, listen, I'm totally with you. Such a special man. The other element that I wanted to ask is you stayed in stealth for quite a while. What are your thoughts on the benefits of stealth and the pros and cons? And how you advise founders on whether to be stealth or not stealth?
25:04 Speaker 03 Yeah, we didn't really choose to be in stealth. Jeff and I, we just chose not to talk about the product until it was ready for customers. So we always advise companies to only do announcements when there's a rational reason for the company to harness the resulting attention of the press. So if you're announcing something just to announce, just so you can see your name in the news or ego booze or to make your parents proud or things like that, those are very easy. Easy quicksand to fall into first time founders, for instance. They think that's a sign of achieving it. What really happens is you get a spike and you really want to have the mechanisms in place for your company to capture that spike or capture that interest. So in our case, the space is really complex. And so we're very product focused, as you can tell.
25:44 Speaker 03 So we took the time to build the product with the intense care and intense focus that we believe products should be. So now after two years of that intense development and we can finally announce it, we are now at a point to announce it. And so we have earlier, in this case, last week, and this ready for us to let in companies more broadly.
26:02 Harry Stebbings? Yeah, no, listen, I totally agree. The final element I have to ask, slightly self-serving probably, but you also chose some incredible angels. I'm not including myself in that when I said that, but some incredible angels. I mean, truly, when you look at it, the best of the best. What was the thoughts around that strategy? Because I think there's seventy two angels from some of the leading companies of the last decade. What were the thoughts around that inclusion of the angels in that respect?
26:23 Speaker 02 Yeah, so the strategy there was from the moment we knew that we were building a product for founders to help them run their businesses, we really wanted to assemble the best list of founders we could in order to learn from their experience and to get their support in helping vouch for and distribute the product. And so that was sort of the original thesis and we're absolutely honored of yourself included founding this. So yeah, we've been delighted by everyone we were able to get involved.
26:49 Harry Stebbings? Yeah, it's been amazing to see and very touched to be involved. So I absolutely really appreciate that, but I do want to move into my favorite, which is a quickfire round champ. So I say a short statement, you hit me with your immediate thoughts, sixty seconds each. Are you ready to rock and roll?
27:02 Speaker 03 Yes.
27:02 Speaker 02 Sounds good.
27:03 Harry Stebbings? This should be fun. So Wayne, let's start with you on this one and then Jeff. Guys, I'm terrible at reading. What's your favorite book and why?
27:11 Speaker 03 For me, it's Enders Game. I don't want to give away too much because it's part of the endings, but it's an abstraction of a really complex decision making into really simple interfaces.
27:22 Speaker 02 Nice. I would say actually Ken Cosiendo's book Creative Selection, I think it came out a couple of years ago or so. My time I spent at Apple actually overlaps with the period he covers in the book. And the book is stunningly accurate in how it portrays how Apple designed and shipped products. Under Steve Jobs in the mid 2000s. So for anyone who was not working at Apple at that time, I'd highly recommend you read it.
27:42 Harry Stebbings? Jeff, what do you know now that you wish you'd known when you entered the startup world?
27:46 Speaker 02 The people over the tech. I would say you get into the industry thinking, we're going to build great software, right? We're going to invent this next great technology. And what I've really come to realize, the people matter more than anything else. Like, I feel so fortunate that Wayne crashed that dinner, that we got to meet in Boston, that we were very, very thoughtful with how we built the Crash Licks team. And believe it or not, a large portion of that team is now the digits team, and we're still working together nine years later. And so it's just, yeah, the people are everything.
28:13 Harry Stebbings? Can I ask one that's not in the quickfire? And it's to either, but I'm really interested because it's so obvious with you guys. What makes you guys work so well together? Because the chemistry is so inherent. But what drives that, do you think?
28:24 Speaker 03 There's an intense amount of trust and respect that I have for Jeff. And so for the first time, I'm able to just worry about what's best for customers. I don't need to think about the deep engineering and tech and all that goes away, which remains for me, that removes all the boundaries and all the limitations for crafting great product experiences for customers. And I'm really grateful. And every day I wake up and I'm like, this is going to be a great day. And one of the things I'm really thankful is like, I have a partner in Jeff. And it's almost 10 years now. And I'm so grateful.
28:54 Speaker 02 Yeah, and I would echo that. Like, that's exactly it. It's basically, we completely trust each other with our sides of the business. And we sort of meet in the middle on product. And so from my point of view, like, I'm obsessed with the technology and the product and building it. I'm not very good at bringing it to market. But now I can fully and completely trust Wayne to distribute the product, get customers to love it, build obsessive fans, etc. And so it's just freeing in our focus.
29:19 Harry Stebbings? I mean, there's so much love in this episode. I feel I don't need to watch Love Actually for a couple of weeks. Okay, Wayne, tell me, what's your superpower? And then your weakness in company building? 30 seconds on each.
29:29 Speaker 03 My North Star, as you can tell, is just, is purely customers. And that means for me, you know, I feel very fortunate that I get to focus on building these product experiences from the moment that people hear about the company, all the way through to getting them to be a repeat customer and loving this. And my weakness, because I care so intensely about the seamless experience with customers, delegation becomes an ongoing battle, because I want to have a tight reign on making each experience perfect and each one unique in its own ways. That's really important to me.
29:58 Harry Stebbings? Jeff, what would you most like to change about the world of Ventures Day? Hit me. I'm a VC. I need help. What can we change about this world?
30:05 Speaker 02 Well, it's funny, and I think Wayne and I might have a sort of unique perspective on this. So we not only have obviously taken investor money for digits. We also are very active angel investors and we're also LPs in, I think, eight different VC firms right now. And so we sort of get to see this industry from all sides. And I would say from every side, the biggest challenge is still visibility. Like, it's incredibly difficult, not only for the founder to know how their business is doing, but for the investors to actually value their private company investments. And so this is why, like, every angel I know has an outdated spreadsheet somewhere that they think tries to track their portfolio, but it's incorrect. And every VC firm has to pay for quarterly reports, but they all value the same companies differently. And their reports are very basic and yet still hard to read.
30:49 Speaker 02 And so we don't have the solution yet. It's definitely a tricky problem, but I'd love for there to be far better tooling and better transparency in sort of the venture world across the tech industry.
30:58 Harry Stebbings? I totally agree with you there. I think it's still crazy that we have that, to be honest. So totally aligned there. Wayne, hit me. Who was the first jack into digits and how did that come about?
31:07 Speaker 03 We were fortunate to find ourselves in a situation where we had a lot of entrepreneurs and founders that wanted to be part of this journey. The moment that we found out that we're going to be building a product for founders, boy, we got a lot of others on board as fast as we could. We ended up with 72. And this gives us 72 different perspectives to build out the product for. And we want to be able to support different industries. And those 72 represented 35 of the broadest industries that we could find. So we're very fortunate to be able to have those angels join us on this journey.
31:37 Harry Stebbings? Jeff, again, help me. What's the single most important way a VC can be helpful?
31:41 Speaker 02 I would say by drawing your attention to what's important, but not urgent. So it's been funny because all these VCs over the past few years have touted value-added services in other parts of the business and they can recruit for you and do these other things for you. I actually, I don't need the investors to do stuff for us, right? Like, as an operator, your job is to execute. Your job is to operate. I'm fine with that. What I think is most helpful is when the investors are always looking forward because they're not caught up in the day-to-day. And many founders get so caught up in the day-to-day, they're context switching, they're racing between fires, that they sort of Lose track of what's important in the bigger picture. And so to me, a great face city is basically always looking forward for their company, drawing the founders to spend time on what's really important,
32:25 Speaker 02 even if it's not the most urgent thing right now, and sort of coaching them on how to be more strategic.
32:30 Harry Stebbings? Wayne, penultimate one. When I say success, who's the first person that comes to mind?
32:34 Speaker 03 I'm gonna say an obvious answer, but not for the reason why you think. I'm gonna say Warren Buffett, but not because of his wealth, but because of the way he defines success. So in work, he optimizes for a calendar that has very few committed meeting blocks. Yet, all the things he needs and wants to get done, they're done. So this means he has full mastery over his own time. So I feel like that's really successful in terms of work and your schedule. The way he defines success at the end of life, not by wealth or anything materialistic, but by the number of people around you that care about you. So for me, business is really just a giant game that we're all playing together. And keep me out of mind really gives me perspective on what's really important.
33:13 Harry Stebbings? Yeah, I'm always intensely jealous of people like that.
33:17 Harry Stebbings? Tell me, guys, this is the toughest of all, but the most exciting of all. What are the next five years hold for you and for Digits? Like, paint the roadmap. When all goes well, what does this look like?
33:25 Speaker 03 I'm gonna be a little bit reflective here, but for me, I hope I'm still fortunate enough to do the things that I love to do, which is to create these new product experiences that can delight, empower the next generation of companies. There should be no reason why the software that you use to exercise, the software you use to entertain yourself, why are those way more powerful and delightful than the software you use to work? So I hope that in five years, I'll be able to continue to work on this problem and continue to change that norm and make a new norm.
33:55 Speaker 02 Yeah, I would echo that. I'd say what draws me to this problem space is that it applies to everyone who runs a business. This is like perfectly horizontal. I've never met a founder who looked at a P and L and was like, yes, now I know what to do. And so, right from there, you know there's a problem. And so, of course, that means that we have an opportunity. Every business owner wants to make their company stronger. They're just missing the right tools. And so honestly, I would say in five years, I want Digits to be at the heart of every business of every size on earth. I think there's a huge potential for basically operationalized finance.
34:26 Harry Stebbings? Guys, as you know, I've wanted to see this one for a long time. I'm so pleased that you guys are finally out of stealth and out of quiet mode. This has been so much fun, and thank you so much for joining me again.
34:34 Speaker 02 Thank you so much for having us. It's always great fun to hang with you.
34:38 Speaker 03 Same. Thank you so much.
34:41 Harry Stebbings? I have to say, I just couldn't be more excited for the journey ahead with Digits and for Wayne and Jeff. And if you'd like to see more from them, you can find Wayne and Jeff on Twitter @Wayne and @JeffCybert. Likewise, it'd be great to welcome you behind the scenes here. You can do so on Instagram at HStubbings1996 with two Bs. However, before we leave you today, I'm sure you've heard about it, but my word, this is a product I love: Carter. Carter simplifies how startups and investors manage equity, track cap tables and get valuations. Go to Carter.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carter to manage hundreds of billions of dollars in equity, and Carter now offers fund administration. So you can see real-time data in the Carter platform
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36:49 Harry Stebbings? episode on Monday with the one and only Mark Cuban.
Previous 20VC: Airtable's Howie Liu on Potential Consolidation In The Collaboration Tools Market, The Transition From Peacetime To Wartime CEO & How To Make The Move To Remote Work Successful; The Process Beyond The Tools Next 20VC: Mark Cuban on His Relationship To Wealth and Risk, Why Coming Out of The Pandemic Will Be The Best Time In The History of Mankind To Start A Business & Why Silicon Valley Investors Are Like Old Hollywood Page updated October 26, 2026 · transcript and summary are machine-generated
